In certain early publications dealing with polyketone compositions, it was suggested that polyoximes can be formed by the reaction of a polyketone with hydroxylamine. For example, M. M. Brubaker et al. in J. of the Amer. Chem. Soc., Vol. 74, pp. 1509-1515, describes certain free radical initiated-polyketone compositions formed by polymerizing carbon monoxide and ethylene which could be formed into polyoximes by reaction with hydroxylamine. These polyketone compositions are quite dissimilar from the linear, alternating polyketones more recently developed, and the Brubaker et al. publication merely covers the possibility of copolymerizing ethylene with carbon monoxide. The polyoxime that was formed by Brubaker had 78% of its carbonyl groups converted to oxime groups. This polyoxime was insoluble in water.
A more recent publication by S. J. Kim et al. in Die Makromolekulare Chemie, 175, 125-136 (1974), also describes polyketones of carbon monoxide and ethylene Which are indicated as being synthesized by a method similar to that used by Brubaker et al. In this publication the polyoximes are said to be soluble only in mixtures of organic solvents such as ethanol/dioxane or ethanol/acetone. They are indicated as also dissolving both in mineral acid and base, such as more than 10% aqueous sulfuric acid, aqueous sodium carbonate, sodium hydroxide, and the like.
More recently, in European Patent Publication No. 372,602, certain thermoset resins are described which are obtained by curing a thermoplastic polymer which can be obtained by reacting a curing agent with a linear, alternating copolymer of carbon monoxide and one or more olefinically unsaturated compounds. Although this patent lists propene as one possible monomer that can be used in forming the polyketone compositions that it teaches can be converted to other structures, no actual examples of conversion of a carbon monoxide-propylene polyketone to a polyoxime are actually shown in this patent.